Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors

ABSTRACT

Gemini surfactants of bis-N-alkyl polyether, bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-amino acids or their salts, are produced for use as multifunctional corrosion inhibitors, which protect and prevent corrosion of ferrous metals exposed to acidic, basic and neutral liquids when transporting or storing crude oil and liquid fuels. The surfactants are also used to inhibit corrosion of equipment and pipes used in cooling systems in petroleum and petrochemical equipment. The Gemini surfactants have the structural formula:

CROSS-REFERENCE TO RELATED APPLICATION

This application is a divisional application of Ser. No. 12/967,520,filed Dec. 14, 2010, now U.S. Pat. No. 8,518,868, which applicationclaims priority to Mexican Patent Application No. MX/a/2009/013704,filed Dec. 15, 2009, which is hereby incorporated by reference in itsentirety.

FIELD OF THE INVENTION

The present invention is related with new gemini surfactantsbis-N-alkylpolyether, bis-N-alkenylpolyether, bis-N-cycloalkylpolyetheror bis-N-arylpolyether bis-beta or alpha amino acids or their salts, aprocess for producing the surfactants and use principally asmultifunctional corrosion inhibitors, which protect and prevent ofcorrosion of:

-   -   Ferrous metals that transported or stored crude oil and liquid        fuels as primary fuel without desulfurizing, gasoline with low        sulfur content, alkylated gasoline, jet fuel, diesel and MTBE,        by the presence of acidic pollutants, sulfur compounds and        water, exposed or not to oxygen, and    -   Equipment and pipes used in cooling systems that use water        characterized by a high concentration of divalent ions such as        calcium and magnesium which are the main cause of producing        pitting corrosion in this environment.

The gemini surfactants of the present invention and their formulations,have the characteristic of having a low environmental impact.

BACKGROUND OF THE INVENTION

In the oil industry throughout its supply chain there are severalproblems that cause daily losses of millions caused by falls in crudeoil production, as well as failures caused by wear of pipelines andequipment, predominantly from corrosion problems, because of this isthat globally the investigations are aimed at generating solutionsthrough a variety of methods to minimize such problems.

Corrosion is a phenomenon that causes millions in losses in the oilindustry, because it occurs in virtually all oil production chain fromfarm to processing it.

Corrosion is considered the progressive wear of a metallic material dueto its interaction with the surrounding environment.

Corrosion taking place in environments characteristic of the petroleumindustry can be caused by a large number of pollutants, among whichhydrogen sulfide, carbon dioxide, organic acids, inorganic salts such assodium chloride, ammonium cyanide, scales as barium sulfate, calciumcarbonate, strontium sulfate and calcium sulfate and hydrochloric acid,among others, these pollutants cause loss of metallic material byuniform corrosion and pitting which can lead to serious accidents.

The corrosion phenomenon is also commonly found in transportation andstorage of products derived from oil refining as gasoline withoutdesulfurize, gasoline with low sulfur, diesel, alkylated gasoline, jetfuel, diesel and methyl tert butyl ether, from others.

The main damage caused by internal corrosion is uniform wear of thematerial, mainly due to the formation of iron sulfides and chlorides.

For the particular case of the services area, especially in coolingsystems, the high concentration of divalent ions such as calcium andmagnesium in the water used is the main factor of wear of piping andequipment, and accidents due to pitting corrosion. In this regard, it isimportant to note that both globally and in Mexico there is a tendencyof increasing the production of heavy crude oils, which generally have ahigher content of pollutants, as well as environmental regulations thatincreasingly restrict the use of water, the concentration of divalentions such as calcium and magnesium is increased by evaporation of waterlost to the environment, caused by heat exchange with other processfluids.

Because of this, the global trend in the area of chemicals is thedevelopment of corrosion inhibitors with a greater degree ofversatility, capable of controlling the corrosion levels despitesignificant increases in contaminants in crude oil, fuel and water usedin the process, which imparts a more aggressive characteristic.

Gemini surfactants are a family that is characterized by having in theirmolecules at least two hydrocarbon chains and two hydrophilic or polargroups:

whereas the conventional surfactant molecules contain one or twohydrocarbon chains attached to the same polar group.

In this regard, most of the gemini surfactants in their molecules have ahydrocarbon chain, a polar group, a short hydrocarbon chain that acts asa bridge or spacer, a second polar group and a hydrocarbon chain.

The first synthesis of gemini surfactants was announced in 1971 by C. A.Bunton, L. Robinson, J. Schaak, M. F. Stam, University of California,who called them dication detergents. These researchers used geminicationic surfactants as catalysts for certain reactions of nucleophilicsubstitution. The successive names taking these substances werebis-quaternary ammonium surfactants, dimeric surfactants, geminisurfactants and siamese surfactants.

In most of the gemini surfactants, the polar groups are ionic (cationic,anionic and, less frequently, amphoteric), but also synthesizedsurfactants with nonionic polar groups formed by polyethers. In thepioneering work of Bunton, Robinson, Schaak and Stam, the shorthydrocarbon chain that acts as a bridge and linking the two parts ofsurfactant, each of which is consisting of a polar group, in this case acation and a lipophilic chain.

Representative examples of new processes for obtaining geminisurfactants are:

-   -   U.S. Pat. No. 5,945,393 (A), issued Aug. 31, 1999, discloses        obtaining gemini non-ionic surfactants based on alkyl        phosphonates or sulfonates or alkyl aryl polyethers, and its        application in the formulation of detergents and personal        hygiene products.    -   U.S. Pat. No. 5,952,290 (A), issued Sep. 14, 1999, discloses        obtaining base anionic gemini surfactants alkyl amides or alkyl        aryl sulphonated and its application in the formulation of        detergents and personal hygiene products.    -   U.S. Patent Publication No. 2003/078176 (A1), published Apr. 24,        2003, discloses obtaining surfactants with long chain alcohols        and polyether derivatives of ethylene oxide and its application        in detergent formulation.    -   U.S. Patent Publication No. 2003/078182 (A1), published Apr. 24,        2003, discloses obtaining base compositions of gemini        surfactants 1,2-epoxy-alkane where the alkyl groups may be        linear or branched, polyols derived from ethylene oxide and its        application in detergents.    -   U.S. Patent Publication No. 2009/054368 (A1), published Feb. 26,        2009, discloses obtaining gemini surfactants quaternary amine        base substituted alkyl or aryl groups such as pyrene and its        application in the controlled release of active biological        agents such as nucleic acids.

Representative examples of corrosion inhibitors used in acidenvironments of the oil industry are:

-   -   U.S. Pat. No. 3,623,979 (A), issued Nov. 30, 1971, relates to        obtaining a base compound aminoalkyl-2-alkyl imidazolines and        their use as corrosion inhibitors for ferrous metals in acidic        characteristic of the oil industry. The efficiency of corrosion        inhibition of these compounds was evaluated by gravimetric        techniques.    -   U.S. Pat. No. 3,629,104 (A), issued Dec. 21, 1971, relates to        the procurement of organic acid salts of compounds derived base        1-aminoalkyl-2-alkyl imidazolines and their use as corrosion        inhibitors for ferrous metals in acidic characteristic of the        oil industry. The efficiency of corrosion inhibition of these        compounds was evaluated by gravimetric techniques    -   U.S. Pat. No. 3,390,085 (A), issued Jun. 25, 1968, relates to a        mixture containing an imidazoline salt prepared from the        reaction of a fatty acid having 6 to 18 carbons with imidazoline        selected from the group consisting of        1-aminoalkyl-2-alkyl-imidazoline and 1-hydroxyalkyl-2-alkyl        imidazolines and their application as corrosion inhibitors in        acidic characteristic of the oil industry.    -   U.S. Pat. No. 4,388,214 (A), issued Jun. 14, 1983, relates to        corrosion inhibitors synthesized from the reaction of        imidazoline salts and imidazolines with sulfur. These compounds        are particularly useful for inhibiting corrosion of metal        containers caused by carbon dioxide and hydrogen sulfide during        transport and storage of crude oil.    -   U.S. Pat. No. 5,062,992 (A), issued Nov. 5, 1991, relates to a        corrosion inhibiting formulation for oil and water systems,        wherein the formulation is resistant to sludge formation and        tends to stabilize oil in water. The corrosion inhibitor        includes an imidazoline dissolved in an aromatic solvent, a        2-hydroxyalkyl carboxylic acid and glycol. The imidazoline is        preferably prepared from the reaction of a long chain fatty acid        and a polyamine.

Representative examples of corrosion inhibitors used in piping, tanksand other combustible handlers are:

-   -   U.S. Pat. No. 4,214,876 (A) (Corrosion inhibiting composition),        issued Jul. 29, 1980, relates to the development of a        formulation of the corrosion inhibition for ferrous metals        exposed to hydrocarbon fuels comprising 75-95 weight percent of        an unsaturated aliphatic carboxylic acid 16 to 18 carbons and 5        to 25 weight percent of succinic acid with a monoalkenyl chain        in the range of 8 to 18 carbons, and use of a solvent        hydrocarbon.    -   U.S. Pat. No. 4,509,951 (A) (Corrosion inhibitor for        alcohol-based fuels and gasoline-alcohol mixtures), issued Apr.        9, 1985, relates to the development of a formulation of the        corrosion inhibition for ferrous metals exposed to liquid fuels        based in alcohol or gasoline-alcohol mixtures consisting of        aliphatic carboxylic acid polyunsaturated with 18 carbons, and        the reaction product of a polyamine with an alkenyl        monounsaturated carboxylic acid or aliphatic or alkenyl succinic        anhydride from 8 to 30 carbons.    -   U.S. Pat. No. 4,511,366 (A) (Liquid fuels and concentrates        containing corrosion inhibitors), issued Apr. 16, 1985, relates        to the development of a formulation of the corrosion inhibition        for ferrous metals exposed to liquid alcohol-based fuel or        gasoline-alcohol mixtures composed of an aliphatic carboxylic        acid polyunsaturated 16 to 18 carbons and an alkenyl polyamine.    -   U.S. Pat. No. 4,737,159 (A) (Corrosion inhibitor for liquid        fuels), issued Apr. 12, 1988, relates to the development of a        formulation of the corrosion inhibition for ferrous metals        exposed to liquid hydrocarbon fuels comprising 35-70 weight        percent of monoalkenyl succinic acid with a chain from 8 to 18        carbons and 30 to 65 weight percent of an aliphatic or        cycloaliphatic amine containing from 2 to 12 carbons and        solvents, aromatic hydrocarbon compounds and alcohols of 1 to 4        carbons.

Representative examples of corrosion inhibitors used in cooling systemsinclude:

-   -   U.S. Pat. No. 3,974,090 (A), issued Aug. 10, 1976, relates to        obtaining alkali metal phosphonates and their application as        corrosion inhibitors for cooling systems that use water with        high content of divalent ions such as calcium and magnesium.    -   U.S. Pat. No. 4,003,842 (A), issued Jan. 18, 1977, relates to        obtaining base compounds phosphonates, sulfonates and        carboxylates derived from aliphatic alcohols and polyether        derivatives of ethylene oxide and its application as corrosion        inhibitors in cooling systems.    -   WO 00/30985 (A2), published on Jun. 2, 2000, relates to        obtaining amino-phosphonates based compounds and use as        corrosion and fouling inhibitors in cooling systems.    -   U.S. Pat. No. 4,234,511 (A), issued Nov. 18, 1980, relates to        obtaining base compounds di-alkyl amino phosphonates and their        application as corrosion inhibitors in aqueous systems and        cooling towers.    -   U.S. Pat. No. 6,215,013 (B1), issued Apr. 10, 2001, relates to        the obtaining of bisphosphonic acids and derivatives and their        use as corrosion inhibitors in cooling systems present in the        chemical industry.    -   U.S. Pat. No. 6,572,789 (B1), issued Jun. 3, 2003, relates to        obtaining oligomers phosphine-succinic acid and their        application as corrosion inhibitors in aqueous systems such as        cooling towers.

SUMMARY OF THE INVENTION

The disadvantages of the prior compounds and processes are overcome bythe present invention. The invention is directed to novel geminisurfactants bis-N-alkyl polyether, bis-N-alkenyl polyether,bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-aminoacids or their salts, a production process for producing thesurfactants, and the use of the surfactants as multifunctional corrosioninhibitors.

It is therefore an object of this invention to provide new geminisurfactants of bis-N-alkyl polyether, bis-N-alkenyl polyether,bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-aminoacids or their salts.

An additional object of this invention is to provide the process forobtaining new gemini surfactants of bis-N-alkyl polyether, bis-N-alkenylpolyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta oralpha-amino acids or their salts.

Another object of this invention is to provide an alternative use of thenew gemini surfactants bis-N-alkyl polyether, bis-N-alkenyl polyether,bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-aminoacids or their salts as corrosion inhibitors of ferrous multifunctionalfound in contact with crude oil, hydrogen sulfide, carbon dioxide,cyanides, fuel liquids, brines saturated inorganic salts such as sodiumchloride, calcium carbonate, calcium sulfate, strontium and bariumsulfates and water with a high content of divalent ions such as calciumand magnesium, which is commonly used in cooling systems.

The features of the invention are attained by providing geminisurfactants bis-N-alkyl polyether, bis-N-alkenyl polyether,bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta or alpha-aminoacids or their salts having the formula:

where:

-   -   R₁ is a radical represented by —H or —CH₃,    -   R₂ is an alkyl, alkenyl chain, cycloalkyl or aryl;    -   R₃ is a radical represented by —H, —CH₃, —CH═CH—CH₃, or —COOX;    -   R₄ is a radical represented by —H, —CH₃, or —CH₂—COOX;    -   R₅ is a radical represented by —H, an alkyl, alkenyl,        cycloalkyl, aryl group, or a metal;    -   R₆ is a radical represented by an alkyl, alkenyl, cycloalkyl, or        aryl group;    -   n and m can have values from 1 to 250, depending on the        molecular weight of polyether used, and    -   i can have values of 0 and 1:        -   when i=1:            -   R₃ is a radical represented by —H, —CH₃, —CH═CH—CH₃, or                —COOX, and        -   when i is equal to 0:            -   R₃ is a radical represented by —COOX.

In the radical —COOX used in R₃ and R₄, X is represented by:

-   -   —H, an alkyl, alkenyl group, a cycloalkyl or aryl group, or a        metal.

The invention is also directed to a method of inhibiting corrosion offerrous metals in contact with a liquid selected from the groupconsisting of crude oil, liquid fuels and cooling water, said methodcomprising adding a corrosion inhibitor to said liquid, said corrosioninhibitor comprising gemini surfactants bis-N-alkyl polyether,bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-arylpolyether bis-beta or alpha-amino acids or their salts of the presentinvention as multifunctional corrosion inhibitors to protect and preventcorrosion of the ferrous metals exposed to acidic, basic and neutralenvironments where the surfactant is included at a concentration of 0.5to 10,000 ppm based on the amount of the liquid.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 shows the testing device used by the NACE TM-0172 method, todetermine the efficiency of corrosion inhibition by new geminisurfactants of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is related with new gemini surfactants bis-N-alkylpolyether, bis-N-alkenyl polyether, bis-N-cycloalkyl polyether,bis-N-aryl polyether bis-beta or alpha-amino acids or their salts, aprocess for producing the surfactants and the use of the surfactantsprincipally as multifunctional corrosion inhibitors, which protect andprevent of corrosion of:

-   -   Ferrous metals that are used to transport or store crude oil and        liquid fuels as primary fuel without desulfurizing, gasoline        with low sulfur content, alkylated gasoline, jet fuel, diesel        and MTBE, by the presence of acidic pollutants, sulfur compounds        and water, exposed or not to oxygen, and    -   Equipment and pipes used in cooling systems that use water        characterized by a high content of divalent ions such as calcium        and magnesium that are the main cause of producing pitting        corrosion in this environment.

The gemini surfactants of the present invention and their formulations,have the characteristic of present low environmental impact.

The multifunctional corrosion inhibitors of the present invention relateto the new gemini surfactants bis-N-alkyl polyether, bis-N-alkenylpolyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta oralpha-amino acids or their salts, using distilled water as a solvent orbrine with high content of divalent ions such as calcium, magnesium,strontium or barium, organic solvents or compounds derived from alcoholssuch as methanol, ethanol, isopropanol or mixtures thereof, or aromaticssuch as xylene, toluene, diesel, gasoline or mixtures thereof.

The new gemini surfactants bis-N-alkyl polyether, bis-N-alkenylpolyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta oralpha-amino acids or their salts of this invention have the structuralformula:

where:

-   -   R₁ is a radical represented by —H or —CH₃,    -   R₂ is a alkyl or alkenyl chain, linear or branched, preferably        having 1 to 30 carbon atoms, or an cycloalkyl or aryl group,        preferably having 5 to 12 carbon atoms;    -   R₃ is a radical represented by —H, —CH₃, —CH═CH—CH₃, —COOX;    -   R₄ is a radical represented by —H, —CH₃ or —CH₂, —COOX;    -   R₅ is a radical represented by —H; an alkyl or alkenyl chain,        that is linear or branched, preferably having 1 to 30 carbon        atoms, a cycloalkyl or aryl group, preferably having 5 to 12        carbon atoms, or a metal, preferably being Na, K, Ca, Mg or Cs;    -   R₆ is a radical represented by a linear or branched alkyl or        alkenyl chain, preferably having 1 to 30 carbon atoms, or a        cycloalkyl or aryl group preferably having 5 to 12 carbon atoms;    -   n and m can have values from 1 to 250, depending on the        molecular weight of polyether used, where the polyether used        preferably is derived from ethylene oxide or propylene oxide or        their copolymer whose molecular weight is in the range 100 to        20,000 g/mol; and    -   i can have values of 0 and 1:        -   when i=1:            -   R₃ is a radical represented by —H, —CH₃, —CH═CH—CH₃,                —COOX; and        -   when i=0:            -   R₃ is a radical represented by —COOX.

In the radical —COOX in R₃ and R₄, X are represented by:

-   -   —H; a linear or branched alkyl or alkenyl chain, preferably        having 1 to 30 carbon atoms, a cycloalkyl or aryl group,        preferably having 5 to 12 carbon atoms, or a metal, preferably        being Na, K, Ca, Mg or Cs.

The invention is also directed to a method of inhibiting or preventingcorrosion of metals and particularly ferrous metal using the geminisurfactants as a corrosion inhibitor by contacting the metal with thecorrosion inhibitor. The corrosion inhibitor of the invention caninclude about 1 to 100 wt % of one or more of the gemini surfactants.The corrosion inhibitor containing the gemini surfactants can include asolvent such as water, distilled water, an aqueous brine solution or anorganic solvent. The aqueous brine solution can contain a highconcentration of divalent metal ions such as calcium, strontium, orbarium. The organic solvent can be an alcohol such as methanol, ethanol,isopropanol or mixtures thereof. The organic solvent can also be anaromatic compound such as xylene, toluene, diesel fuel, gasoline ormixtures thereof.

The method of the invention can inhibit or prevent corrosion ofequipment or prevent corrosion of equipment used for storing ortransporting crude oil, liquid fuels and petroleum distillate such aspipelines and storage tanks. The method adds a corrosion inhibitingeffective amount of the gemini surfactants of the invention to the crudeoil, liquid fuel or petroleum distillates. Preferably, the geminisurfactants are included in an amount of about 0.5 ppm to about 10,000ppm based on the amount of the crude oil, liquid fuel or petroleumdistillate. The crude oil, liquid fuel or petroleum distillatecontaining the corrosion inhibitor is then passed through the equipmentor pipeline.

The gemini surfactants are also suitable for use as corrosion inhibitorsin cooling liquids and particularly aqueous cooling liquids for coolingmachinery and various components used in the oil petrochemical andchemistical industries. In one embodiment of the invention, the methodadds at least one of the gemini surfactants of the invention to anaqueous cooling fluid in an amount effective to inhibit or preventcorrosion of the machinery or components. Typically, the geminisurfactants are included in an amount of about 0.5 ppm to about 10,000ppm.

The new gemini surfactants bis-N-alkyl polyether, bis-N-alkenylpolyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta oralpha-amino acids or their salts, of structural Formula XII, areprepared according to the following synthesis scheme:

The reaction scheme of new gemini surfactants bis-N-alkyl polyether,bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-arylpolyether bis-beta or alpha-amino acids or their salts of structuralformula XII, comprises three reaction steps:

-   I. The first stage of the reaction synthesis scheme is to obtain    secondary amines of formula VIII bis-N-alkyl polyether,    bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-aryl    polyether, which can be done through two routes of synthesis:    -   i. The first synthetic route is the formation of diamides of        formula III, by reacting polyethers of formula I, preferably        derived from ethylene oxide or propylene oxide or copolymers of        these with two amino groups, one at the end and another at the        beginning of the polymer chain whose molecular weight is in the        range of 100 to 20,000 g/mol, with compounds of formula II,        where A is derived from carboxylic acids, esters, halide alkyl        or linear or branched alkenyl, preferably having 1 to 30 carbon        atoms, or cycloalkyl or aryl, preferably having 5 to 12 carbon        atoms; the diamides of formula III are reduced to their        corresponding secondary amines of formula VIII using hydrides,        preferably lithium aluminum hydride, or catalytic hydrogenation.    -   ii. The second route of synthesis consists of two stages:        -   The first step is to react polyalkyleneglycols of Formula            IV, preferably derived from ethylene oxide and propylene            oxide or copolymers of these having two hydroxyl groups, one            at the end and the other at the beginning of the polymer            chain whose molecular weight is in the range of 100 to            20,000 g/mol, with at least one of the compounds represented            by the letter B: tosyl chloride, mesyl chloride, bromine or            chlorine molecules, or penta or tri chloride or bromide            phosphorous, preferably chloride tosyl, where the reaction            is carried out with a molar ratio of polyglycols of Formula            IV and B compounds of 1:2 to 1:4, preferably 1:2.2 to 1:2.6,            with alkaline sodium potassium or cesium hydroxide,            preferably sodium hydroxide, using water as a solvent,            tetrahydrofuran or acetonitrile or mixtures thereof, a            reaction time of 1 to 8 hours, preferably 3 to 5 hours at a            temperature of 0 to 25° C., preferably from 5 to 20° C., to            form compounds of Formula VI; and        -   The second step consists of reacting the compounds of            Formula VI via nucleophilic substitution with compounds of            Formula VII: linear or branched alkyl or alkenyl amines,            preferably having 1 to 30 carbon atoms, or cycloalkyl or            aryl, preferably having 5 to 12 carbon atoms, wherein the            reaction is carried out with a molar ratio between the            compounds of Formula VI and VII of 1:1.5 to 1:4, preferably            1:1.8 to 1:2.6, in the presence of solvents such as            acetonitrile, dimethylformamide, dimethylsulfoxide, acetone            or short chain alcohols, preferably acetonitrile, at a            reaction time of 1 to 10 hours, preferably 4 to 6 hours, and            at a temperature of 60 to 100° C., preferably 70 to 85° C.;            to obtain secondary amines of Formula VIII.-   II. The second stage of reaction synthesis scheme is to obtain    compounds of Formula X: bis-N-alkyl polyether, bis-N-alkenyl    polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta    or alpha-amino acids or their salts, which are obtained by reacting    secondary amines of Formula VIII with compounds of Formula IX:    unsaturated acids such as acrylic, methacrylic, itaconic, crotonic,    fumaric, isocrotonic, angelic and maleic acids, among others, alpha    or beta acids or halogenated as chloro-acetic acid, acetic bromine,    bromine and chlorine propionic, or salts of the above acids, or    unsaturated esters such as methyl acrylate and methyl methacrylate,    among others, in which the reaction is carried out with respect    molar among the compounds of Formula VIII and IX of 1:1.5 to 1:4,    preferably 1:1.8 to 1:2.6. The reaction can be carried out in the    absence or presence of solvents such as water, alcohols, aromatic    hydrocarbon solvents or inert solvents, preferably water, toluene or    xylene mixtures, o-xylene, m-xylene, p-xylene, kerosene and jet    fuel. The reaction time, temperature and pressure depend on the    structure of the compounds of Formula VIII and IX. Usually the    reaction time varies from 1 to 24 hours, preferably 1 to 10 hours.    The temperature ranges from 40 to 180° C., preferably 80 to 130° C.,    and the pressure is generally atmospheric, and can vary from 585 to    760 mmHg. The compounds of Formula X can be neutralized with bases    such as hydroxides, carbonates or bicarbonates of sodium, potassium    or cesium.-   III. Finally, the third stage of reaction synthesis scheme is to    obtain compounds of structural Formula XII, which corresponds to the    new gemini surfactants bis-N-alkyl polyether, bis-N-alkenyl    polyether, bis-N-cycloalkyl polyether, bis-N-aryl polyether bis-beta    or alpha-amino acids or their salts which are obtained by reacting    compounds of Formula X with compounds of Formula XI: halides such as    bromide, chloride or iodide linear or branched alkyl or alkenyl,    preferably having 1 to 30 carbon atoms, or cycloalkyl or aryl,    preferably having 5 to 12 carbon atoms, with a molar ratio between    the compounds of Formula X and XI of 1:1 to 1:4, preferably 1:1.5 to    1:2.6. The reaction can be carried out in the absence or presence of    solvents such as water, alcohols, aromatic hydrocarbon solvents or    inert solvents, preferably water, toluene or xylene mixtures,    o-xylene, m-xylene, p-xylene, kerosene and jet fuel. The reaction    time, temperature and pressure depend on the structure of the    structures of the compounds of Formula X and XI. The reaction time    usually ranges from 1 to 24 hours, preferably 1 to 10 hours. The    temperature ranges from 15 to 90° C., preferably 25 to 50° C. and    usually at atmospheric pressure, and can vary from 585 to 760 mmHg.

Some practical examples for better understanding of the presentinvention, without limiting its scope, are discussed below.

EXAMPLE 1 Preparation of4,43-di(octadec-9-enyl)-7,10,13,16,19,22,25,28,31,34,37,40-dodecaoxa-4,43-diazahexatetracontane-1,46-dioicacid. (Product 1)

In a 500 ml round bottom balloon flask containing 59 g of an aqueoussolution to 17 weight percent of sodium hydroxide (10 g) were added 50 gof polyethylene glycol whose number average molecular weight is 600g/mol, the mixture stirred for 20 minutes. Then, at room temperature(25° C.) and atmospheric pressure (585 mmHg), very slowly 87 g of asolution of tosyl chloride at 40 weight percent (34.8 g) intetrahydrofuran were added, keeping the temperature below 25° C.throughout the addition. After completion of addition, the reactionmixture was stirred for about an hour at room temperature andatmospheric pressure. Then the reaction mixture was made and extractionof organic phase and evaporated the solvent at reduced pressure, toobtain 74 g of Product A as a viscous clear yellow liquid with a yieldof 98%.

As a second stage of reaction in a 500 ml balloon flask, equipped with amagnetic stirrer and a condenser were added 111 g of acetonitrile, 74 gof Product A, 43 g of oleylamine and 34 g of potassium carbonate. Thereaction mixture was stirred vigorously at reflux temperature andatmospheric pressure for five hours, after which time the reactionmixture was filtered and the solution was evaporated to remove thesolvent under reduced pressure. Finally the crude reaction product wasevaporated to remove the solvent under reduced pressure. The crudereaction product was subjected to a solvent extraction and the organicphase was evaporated under reduced pressure, yielding 81 g of Product Bas a clear liquid viscous yellow with a yield of 92%.

For the third reaction stage in a three-necked round bottom flask of 250ml, equipped with a magnetic stirrer, a dropping funnel, a thermometerand a condenser were added 81 g of Product B at room temperature andatmospheric pressure and 10.6 g of acrylic acid were slowly added. Thereaction mixture was stirred vigorously at a temperature not exceeding100° C. and atmospheric pressure for 3 hours. It is noteworthy that thereaction is exothermic and it is important to keep the reaction below100° C. When the reaction time was completed 89 g of the Product 1 wereobtained as a very viscous clear yellow liquid, with a yield of 95%. Theproduct may or may not be neutralized with an alkaline base such aspotassium or sodium hydroxide, or tertiary amine quarternized usingalkyl or alkenyl or aryl halides such as propyl or benzyl bromide orchloride.

The spectroscopic characteristics output 1 are:

Representative bands of FTIR (cm⁻¹, film): 3449, 3005, 2922, 2853, 1729,1585, 1463, 1349, 1323, 1297, 1246, 1106, 1032, 845.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):5.27, 3.57, 3.09, 2.99, 2.86, 2.54, 2.47, 1.95, 1.19, 0.81.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):174.7, 129.8, 129.5, 72.6, 70.3, 53.1, 51.7, 50.2, 50.0, 32.4, 31.7,29.6, 29.5, 29.3, 27.0, 22.5 and 13.9.

EXAMPLE 2 Preparation of4,31-di(octadec-9-enyl)-7,10,13,16,19,22,25,28-octaoxa-4,31-diazatetratriacontane-1,34-dioicacid. (Product 2)

The Product 2 was obtained under the same scheme of synthesis ofProduct 1. For this product is used a polyethylene glycol with anaverage molecular weight of 400 g/mol.

The spectroscopic characteristics of Product 2 are:

Representative bands of FTIR (cm⁻¹, film): 3445, 3003, 2922, 2853, 1722,1586, 1464, 1350, 1295, 1248, 1105, 947, 847.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):5.26, 3.56, 3.01, 2.98, 2.78, 2.50, 2.47, 1.94, 1.18, 0.80.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):175.1, 129.8, 129.5, 72.6, 70.3, 53.0, 51.7, 50.3, 50.0, 32.4, 31.7,29.5, 29.3, 29.1, 27.0, 22.5 y 13.9.

EXAMPLE 3 Preparation of4,16-di(octadec-9-enyl)-7,10,13-trioxa-4,16-diazanonadecane-1,19-dioicacid. (Product 3)

The Product 3 was obtained under the same scheme of synthesis ofProduct 1. For this product is used a polyethylene glycol with anaverage molecular weight of 200 g/mol.

The spectroscopic characteristics of Product 3 are:

Representative bands of FTIR (cm⁻¹, film): 3442, 3004, 2922, 2852, 1718,1575, 1464, 1351, 1291, 1217, 1119, 965, 833.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):5.30, 3.60, 3.14, 2.99, 2.85, 2.55, 2.51, 1.96, 1.23, 0.84.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):175.0, 129.9, 129.6, 70.6, 53.2, 51.8, 50.2, 50.0, 32.5, 31.8, 29.6,29.4, 29.2, 27.1, 22.6 and 14.0.

EXAMPLE 4 Preparation of4,43-didodecyl-7,10,13,16,19,22,25,28,31,34,37,40-dodecaoxa-4,43-diazahexatetracontane-1,46-dioicacid. (Product 4)

The Product 4 was obtained under the same scheme of synthesis ofProduct 1. For this product is used a polyethylene glycol with anaverage molecular weight of 600 g/mol and dodecylamine.

The spectroscopic characteristics of Product 4 are:

Representative bands of FTIR (cm⁻¹, film): 3446, 2921, 2854, 1723, 1572,1461, 1348, 1291, 1211, 1115, 962, 830.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):3.58, 3.12, 3.03, 2.93, 2.56, 2.47, 1.19, 0.82.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):174.6, 72.4, 70.5, 53.0, 51.6, 50.1, 50.0, 31.7, 29.4, 29.3, 29.1, 26.8,22.5 and 14.0.

EXAMPLE 5 Preparation of4,31-didodecyl-7,10,13,16,19,22,25,28-octaoxa-4,31-diazatetratriacontane-1,34-dioicacid. (Product 5)

The Product 5 was obtained under the same scheme of synthesis ofProduct 1. For this product is used a polyethylene glycol with anaverage molecular weight of 400 g/mol and dodecylamine.

The spectroscopic characteristics of Product 5 are:

Representative bands of FTIR (cm⁻¹, film): 3451, 2929, 2851, 1715, 1568,1462, 1359, 1289, 1114, 961, 832.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):3.58, 3.12, 3.03, 2.93, 2.56, 2.47, 1.19, 0.82.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):174.6, 72.4, 70.5, 53.0, 51.6, 50.1, 50.0, 31.7, 29.4, 29.3, 29.1, 26.8,22.5 and 14.0.

EXAMPLE 6 Preparation of4,16-didodecyl-7,10,13-trioxa-4,16-diazanonadecane-1,19-dioic acid.(Product 6)

The Product 6 was obtained under the same scheme of synthesis ofProduct 1. For this product is used a polyethylene glycol with anaverage molecular weight of 200 g/mol and dodecylamine.

The spectroscopic characteristics of Product 6 are:

Representative bands of FTIR (cm⁻¹, film): 3449, 2924, 2856, 1721, 1567,1456, 1355, 1295, 1214, 1125, 954, 829.

Representative chemical shifts of NMR ¹H (CDCl₃), 200 MHz, δ (ppm):3.50, 3.10, 3.05, 2.84, 2.47, 2.45, 1.14, 0.76.

Representative chemical shifts of NMR ¹³C (CDCl₃), 50 MHz, δ (ppm):174.7, 70.2, 54.3, 54.0, 53.0, 52.3, 31.6, 29.3, 29.2, 29.0, 22.4 and13.8.

Performance Testing of the Gemini Surfactants as Corrosion Inhibitors inVarious Corrosive Environments

To evaluate the efficiency of corrosion inhibition in acidicenvironments, basic and neutral characteristic of the petroleum,petrochemical and chemical industries, were used gravimetric andelectrochemical techniques and methods set out in NACE technicaldocuments 1D NACE-182 and NACE TM-172.

The following describes each test procedures and results.

Determination of the Corrosion Inhibition Efficiency Through NACE 1D-182Method.

For this test using a specimen of 1010 carbon steel with dimensions2,540×1,270 cm×0.025 cm, which is weighed and placed inside a bottlecontaining 180 ml of an emulsion or brine aggressive environmentssimulating acids characteristic of the oil industry, and a certainamount of corrosion inhibitor which can vary from 0 to 500 ppm. Thebottle is sealed and placed in a hole of a wheel having a diameter of58.4 cm that is within a range, and then the oven temperature isincreased to 70° C., while the wheel rotates at 30 rpm for about 46hours. At the end of the test, the specimen is removed from the bottle,washed consecutively with chloroform, acetone, water, a solution ofdiluted hydrochloric acid, a potassium bicarbonate solution with 5 inweight and water, cleaned with wire brushing, rinsed with soap andwater, dried in an oven at 60° C. and reweighed. Depending on weightloss and with reference to a target is calculated efficiency ofcorrosion inhibition, while for the evaluation of the corrosion ratereported in thousandths of an inch per year (mpy) are taken into accountthe following parameters the specimen: a) weight loss, b) area, c)density d) test time.

Gravimetric test commonly called dynamic wheel (Wheel test) is a dynamicprocedure developed for fluids (oil, water and inhibitor) that simulatesthe corrosive environment characteristic of oil production.

Testing Equipment and Reagents:

-   a) Evaluating dynamic for corrosion inhibitors with temperature    controller, stirrer speed of 30 rpm and capacity for 52 bottles of    180 ml.-   b) Bottles of 200 ml of capacity.-   c) Coupon SAE 1010 carbon steel, 2,540×1,270×0.025 cm    (1″×0.5″×0.010″).-   d) Glassware for the preparation of a corrosive environment. This    consist of a glass reactor of 2 liter, equipped with a cooling bath,    mechanical stirrer, bubbler for gas (nitrogen and hydrogen sulfide),    has an outlet connected to two traps in series (the first with    sodium hydroxide in pellet form and the second with another sodium    hydroxide solution 20% in weight), so that hydrogen sulfide does not    contaminate the environment.-   e) Potentiometer for measuring pH.

The test conditions are shown in Table 1, while the composition of thebrine used is shown in Table 2.

TABLE 1 Test Conditions, NACE 1D-182 method. Temperature 70° C. Aqueousmedium Synthetic brine with 600 ± 50 ppm de H₂S Test time 46 hoursOrganic medium Kerosene Volume ratio 90/10 Synthetic brine/organicmedium Test volume 180 ml pH 4 Metals coupons Steel SAE 1010

TABLE 2 Brine composition used, 1D-182 NACE method. Salts Amount (g/l)NaCl 60.0 CaCl₂•H₂O 6.0 MgCl₂•6H₂O 10.48 Na₂SO₄ 3.5Results:

The difference in weight of the coupons before and after being exposedto corrosive liquid for 46 hours is a direct indication of metal lostdue to corrosion.

The efficiency of corrosion inhibition is obtained by comparing thereference coupon wear with the wear of the coupons with corrosioninhibitor at different concentrations, using the following formula:% E=(Vo−V)/V×100where:

-   -   Vo=Corrosion velocity of reference coupon.        -   V=Corrosion velocity of coupon with corrosion inhibitor.

Table 3 shows the results of corrosion rate and efficiency on Products 1to 6 of the present invention, used at different concentrations.

TABLE 3 Corrosion rate and efficiency of Products 1 to 6, at differentconcentrations. Concentration, Corrosion velocity, Efficiency, Product(ppm) (mpy's)* (%) Reference 0 41.6 0 1 10 2.2 94.9 1 25 3.5 91.9 1 502.4 94.5 1 75 2..0 95.2 2 10 5.8 86.4 2 25 4.2 90.1 2 50 2.8 91.4 2 750.6 98.5 3 10 4.6 89.3 3 25 1.4 96.7 3 50 1.4 96.7 3 75 1.6 95.9 4 1032.4 24.3 4 25 26.4 38.2 4 50 5.2 87.9 4 75 2.9 93.0 5 10 19.6 54.0 5 255.7 86.8 5 50 3.3 92.3 5 75 2.2 94.9 6 10 3.1 92.5 6 25 2.9 92.8 6 503.1 92.5 6 75 2.8 93.2 *mpy's: thousandths of an inch per year.

The results presented in Table 3 shows that the efficiency of new geminisurfactants of this invention is above 90% at concentrations above 50ppm. At low concentration (10 ppm), the efficiency depends on size ofthe hydrophobic chains and the size of polyether employed (molecularweight) suggesting that long-chain hydrophobic promotes the repulsion ofwater molecules to the metal surface through a steric effect.

Determination of the Efficiency of Corrosion Inhibition by the MethodNACE TM-0172.

Test Description:

Test Method NACE TM-0172 is to determine the corrosive properties ofgasoline, jet fuel and distillate fuels that found in pipelines andstorage tanks. Also includes information on metal specimen preparations,equipment and a system for ranking the test samples with corrosioninhibitor.

Testing Equipment and Apparatus:

The apparatus consists of:

-   -   A temperature measuring device, and    -   One bath vessel. Should be used a thermally controlled bath of        mineral oil capable of maintaining a temperature in the test        sample 38±1° C. The bath vessel must have a cover with holes to        accommodate the test glass and the temperature measuring device.

The test device used by the NACE TM-0172 method to determine theefficiency of corrosion inhibition posed by gemini surfactants of thepresent invention, illustrated by FIG. 1, consists of a test specimen(A), a digitally controlled stirrer (B), a cover of poly(tetrafluoroethylene) (C), a glass (D) and hydrocarbon-water mixture(E).

The sample must be a steel yarn 81.0×12.7 mm, the steel shall conform toUNS* G10150 (Grade 1015), UNS G10180 (1018), UNS G10200 (1020) or UNSG10250 (1025) ASTM A108, used with a plastic handle ofpoly(tetrafluoroethylene) (PTFE). (* Unified Numbering System).

Test Procedure:

Add 300 ml of fuel to the test vessel and dispensed corrosion inhibitorto the desired concentration. The glass is placed in an oil bath at atemperature of 38±1° C. After 30 minutes of continuous stirring add 30ml of distilled water, and continuous agitation for three hours.Subsequently the sample is removed, and left to drain and washed withtoluene or xylene followed by acetone.

Sample Qualification: The rating should be based solely on the portionof the sample that remained in the test fluid. The corrosion productsformed during the test have had limited opportunity to darken, and alldeposits of solids not removed by washing of toluene and acetone shouldbe considered as products of corrosion. Marks on the circle can occurduring polishing and should not be interpreted as corrosion;classification is based according to Table 4.

TABLE 4 Samples qualification, NACE TM-0172 method. QualificationPercent of corroded surface A 0 B++ Less than 0.1 (2 or 3 spots of nomore than 1 mm in diameter). B+ Less than 5 B 5 a 25 C 25 a 50  D 50 a75  E 75 a 100

Table 5 shows the results of the corrosion inhibition efficiency ofproduct 1 with a variety of liquid fuels, according to NACE TM-0172method.

TABLE NO. 5 Product 1 qualification, when used with a variety of liquidfuels. NACE TM-0172 method. Qualification, Concentration, Test medium,(NACE Product (ppm) (fuel) TM-0172) Reference 0 All fuels E 1 10 Primarygasoline B++ (without desulfurize) 1 10 Magna gasoline A 1 10 Premiumgasoline A 1 10 Diesel B++ 1 10 MTBE A 1 10 Alkylated gasoline A 1 10Magna gasoline/ A Ethanol (50:50)

From the results shown in Table 5 the new Gemini surfactant (Product 1)at low concentration (10 ppm) passes the test with B++ and A, when useda variety of liquid fuels.

Table 6 shows the results of the efficiency of corrosion inhibition bythe Products 2 to 6 of the present invention, when used gasoline withlow sulfur content at different concentrations, according to NACETM-0172 method.

TABLE 6 Qualifications of Products 2 to 6 of the present invention, whenused gasoline with low sulfur content at different concentrations, NACETM-0172 method. Qualification, Concentration, (NACE Product (ppm)TM-0172) Reference 0 E 2 10 B+ 2 25 B++ 3 10 B+ 3 25 A 4 10 B++ 4 25 B++5 10 B+ 5 25 B++ 6 10 B++ 6 25 A

From the results shown in Table 6 that the new gemini surfactants of thepresent invention, at a concentration of 25 ppm pass the test ofcorrosion inhibition with a grade B++ and A. At low concentration (10ppm) only the Products 4 and 6 pass the test.

From the above it is concluded that the efficiency of corrosioninhibition depends on the size of the hydrophobic chains and, for theparticular test, the balance between the size of the spacer or bridgeused and the length of the hydrocarbon chains.

Determination of the Efficiency of Corrosion Inhibition byElectrochemical Techniques.

Equipment Used:

A glass electrochemical cell, reference electrode, working electrode,counter electrode, pH meter, multimeter, potentiostat/galvanostatAutolab PGSTAT 30 71410 were used. A bitter brine of pH 4 was preparedand the dissolution of chemicals in isopropanol in order to preparedissolution of 1,000 ppm in 100 ml.

Test Procedure:

A specimen of carbon steel 1010 with area of 0.5 cm² by grinding with600 grit sandpaper. The bitter brine is the same as was used for thegravimetric technique. Polarization curves were generated linearopen-circuit potential ±25 mV. The polarization curve is obtained andanalyzed to determine the corresponding corrosion rate. To make a newexperiment is necessary to perform the roughing electrode is placed inthe cell and generate another curve. This procedure is repeated untilthere is a coincidence of at least two curves. The experiments wereperformed at room temperature with magnetic stirring and bitter brineadjusted to pH 4.0±1. The corrosion rate (mpy) is determined throughmanipulation of the curve using the program of the potentiostat.

Table 7 shows the results of the corrosion inhibition efficiency by theProducts 1 to 4 of the present invention, at different concentrations,using electrochemical techniques:

TABLE 7 Efficiency of corrosion inhibition of Products 1 to 4, of thepresent invention, at different concentrations, using electrochemicaltechniques Concentration, Corrosion velocity, Efficiency, Product (ppm)(mpy's) (%) Reference 0 72 0 1 25 18 75 1 50 12 83 2 25 21 71 2 50 18 753 25 16 78 3 50 12 83 4 25 16 78 4 50 12 83

From the results shown in Table 7 show that the corrosion inhibitionefficiencies are maintained above 70% at concentrations of 25 and 50ppm, and these concentrations are sufficient to protect the metalsurface of the aggressive environment.

Determination of the Corrosion Inhibition Efficiency in Water of CoolingSystems Present in the Petroleum, Petrochemical and Chemical Industries.

A specimen of 1010 carbon steel with dimensions 2,540×1,270 cm×0.025 cm,which is weighed and placed inside a bottle containing 180 ml of hardwater (high concentration of divalent ions of calcium and magnesium)that simulates the environment of cooling systems present in thepetroleum, petrochemical and chemical industries, and a certain amountof corrosion inhibitor which can vary from 0 to 500 ppm. The bottle issealed and placed in a hole of a wheel having a diameter of 58.4 cm thatis inside an oven. Then the oven temperature is increased to 40° C.,while the wheel rotates at 30 rpm for about 16 hours. At the end of thetest, the specimen is removed from the bottle, washed consecutively withchloroform, acetone, water, a solution of diluted hydrochloric acid, apotassium bicarbonate solution to 5 weight percent and water, cleanedwith wire brushing, rinsed with soap and water, dried in an oven at 60°C. and reweighed. Depending on weight loss and with reference to atarget is calculated efficiency of corrosion inhibition, while for theevaluation of the corrosion rate reported in thousandths of an inch peryear (mpy) are taken into account the following parameters the specimen:a) weight loss, b) area, c) density d) test time.

Gravimetric test is commonly called dynamic wheel (Wheel test) thatsimulates the corrosive environment typical of environments found incooling systems.

The test conditions are shown in Table 8, while the composition of thebrine is shown in Table 9.

TABLE 8 Test Conditions, Corrosion inhibition in water of coolingsystems present in the petroleum, petrochemical and chemical industries.Temperature 60° C. Aqueous medium Synthetic hard water Test time 16hours Test volume 180 ml Medium pH 8.4 Coupon sample Carbon steel SAE1010

TABLE 9 Brine composition, Corrosion inhibition in water of coolingsystems present in the petroleum, petrochemical and chemical industries.Salts Amount, (mg/l) CaCl₂ 360 MgSO₄ 200 NaHCO₃ 100Results:

The difference in weight of the coupons before and after being exposedto corrosive liquid for 16 hours, and the presence of pitting, is adirect indication of metal lost due to corrosion.

Table 10 shows the efficiency results that showed the Products 1 and 2of this invention, used at different concentrations.

TABLE 10 Efficiency of Products 1 and 2 of the present invention, atdifferent concentrations Concentration, Efficiency, Product (ppm) (%)Reference 0 0 1 10 51.4 1 25 73.4 1 50 87.3 1 75 93.1 2 10 26.8 2 2549.5 2 50 78.4 2 75 93.1 Note: None of the coupons showed pitting

From the results shown in Table 10 the Products 1 and 2 have the abilityto inhibit pitting or localized corrosion, providing better results at aconcentration of 75 ppm, due to its solubility in water, mainly throughtwo mechanisms: 1) Formation of film on the metal surface and 2)Formation of coordination complexes with ions in solution to avoidprecipitation.

What is claimed is:
 1. A process for producing bis-N-alkyl polyether,bis-N-alkenyl polyether, bis-N-cycloalkyl polyether, bis-N-arylpolyether bis-beta or alpha-amino acids or their salts having theformula XII

where: R₁ is independently a radical represented by —H or —CH₃, R₂ is analkyl, alkenyl chain, cycloalkyl or aryl; R₃ is a radical represented by—H, —CH₃, —CH═CH—CH₃, or —COOX; R₄ is a radical represented by —H, —CH₃,or —CH₂—COOX; R₅ is a radical represented by —H, an alkyl, alkenyl,cycloalkyl, aryl group, or a metal; R₆ is a radical represented by analkyl, alkenyl, cycloalkyl, or aryl group; n and m can have values from1 to 250, and i can have values of 0 and 1: when i=1: R₃ is a radicalrepresented by —H, —CH₃, —CH═CH—CH₃, or —COOX, and when i is equal to 0:R₃ is a radical represented by —COOX; In the radical —COOX used in R₃and R₄, X is represented by: —H, an alkyl, alkenyl group, a cycloalkylor aryl group, or a metal; wherein said process comprises the reactionscheme

wherein the secondary amine of Formula VIII is reacted with a compoundof Formula IX to obtain the compound of Formula IX to obtain thecompound of Formula X, wherein said compound of Formula IX is selectedfrom the group consisting of unsaturated alpha or beta acids and saltsthereof, halogenated acids and salts thereof, and unsaturated esters,and reacting the resulting compound of Formula X with a compound ofFormula XI, where X is selected from the group consisting of bromide,chloride and iodide, and R₆ is as defined above to obtain the compoundof Formula XII.
 2. The process of claim 1, wherein the ratio of thecompound of Formula VIII to the compound of Formula IX is 1:1.5 to 1:4.3. The process of claim 2, wherein the reaction of the compound ofFormula VIII and the compound of Formula IX is carried out in thepresence of a solvent selected from the group consisting of water,alcohol, and aromatic hydrocarbons at a temperature of 40 to 180° C. andatmospheric pressure.
 4. The process of claim 3, wherein said reactionof the compound of Formula X and said compound of Formula XI is carriedout at a ratio of 1:1 to 1:4.
 5. The process of claim 4, wherein saidreaction of the compound of Formula X and said compound of Formula XI iscarried out at a temperature of 15° C. to 90° C. at a pressure of 585 to760 mmHg.
 6. The process of claim 1, wherein the compound of Formula IXis selected from the group consisting of acrylic acid, methacrylic acid,itaconic acid, crotonic acid, fumaric acid, isocrotonic acid, angelicacid, maleic acid, methyl acrylate and methyl methacrylate.
 7. Theprocess of claim 1, wherein the molar ratio of compounds of Formula VIIIand IX is 1:1.8 to 1:2.6.
 8. The process of claim 1, wherein thecompound of Formula XI is a linear or branched alkyl or alkenyl halideand contains 1 to 30 carbon atoms.
 9. The process of claim 1, whereinthe compound of Formula XI is a cycloalkyl or aryl containing 5 to 12carbon atoms.
 10. The process of claim 1, wherein the molar ratio ofcompounds of Formula X and XI is 1:1.5 to 1:2.6.
 11. The process ofclaim 1, wherein said compound of Formula VIII is obtained by reacting acompound of Formula I with a compound of Formula II to obtain a compoundof Formula III, and thereafter reducing the compound of Formula III toobtain the secondary amine of Formula VIII, according to the followingreaction scheme

where A is selected from the group consisting of carboxylic acid,carboxylic acid ester, alkyl halide, alkenyl halide, cycloalkyl andaryl.
 12. The process of claim 11, wherein said compound of Formula IIIis reduced to the compound of Formula VIII by reacting with a hydride orby catalytic hydrogenation.
 13. The process of claim 11, wherein thecompound of Formula I is a polyether derived from ethylene oxide orpropylene oxide or copolymers thereof with two amino groups, one at aterminal end and the other at a beginning of the polymer chain andhaving a molecular weight in the range of 100 to 20,000 g/mol.
 14. Theprocess of claim 11, wherein A of the compound of Formula II is a linearor branched alkyl or alkenyl halide and contains 1 to 30 carbon atoms.15. The process of claim 1, wherein said compound of Formula VIII isobtained by reacting a compound of Formula IV with a compound B ofFormula V selected from the group consisting of tosyl chloride, mesylchloride, bromine, chlorine, and penta or tri chloride or bromidephosphorous, to obtain the compound of Formula VI, and reacting thecompound of Formula VI by nucleophilic substitution with a compound ofFormula VII to obtain the compound of Formula VIII, according to thereaction scheme

where the compound of Formula VII is selected from the group consistingof alkyl, alkenyl, cycloalkyl and aryl amines.
 16. The process of claim15, wherein said compound of Formula IV and compound B of Formula V arereacted in a ratio of 1:2 to 1:4 with sodium, potassium or cesiumhydroxide at a temperature of 0-25° C.
 17. The process of claim 16,wherein said compound of Formula IV and compound B of Formula V is in asolvent selected from the group consisting of water, tetrahydrofuran,acetonitrile, and mixtures thereof.
 18. The process of claim 17, whereinsaid compound of Formula VI is reacted with said compound of Formula VIIat a ratio of 1:15 to 1:4 at a temperature of 60-100° C.
 19. The processof claim 18, wherein said compound of Formula VI is reacted with saidcompound of Formula VII in a solvent selected from the group consistingof acetonitrile, dimethylformamide, dimethylsulfoxide, acetone and shortchain alcohols.
 20. The process of claim 15, wherein the compound ofFormula IV is a glycol derived from ethylene oxide or propylene oxide orcopolymers thereof with two hydroxyl groups, one at a terminal end andthe other at a beginning of the polymer chain, and has a molecularweight in the range of 100 to 20,000 g/mol.
 21. The process of claim 15,wherein the molar ratio of the compound of Formula IV and compound B ofFormula V is 1:2.2 to 1:2.6.
 22. The process of claim 15, wherein thecompound of Formula VII is linear or branched cycloalkyl or aryl amineand containing 5 to 12 carbon atoms.
 23. The process of claim 15,wherein the molar ratio of compounds of Formula VI and VII is 1:1.8 to1:2.6.
 24. A method of inhibiting corrosion of ferrous metals in contactwith a liquid selected from the group consisting of crude oil, liquidfuels and water, said method comprising adding a corrosion inhibitor tosaid liquid, said corrosion inhibitor comprising a Gemini surfactantbis-N-alkyl polyether, bis-N-alkenyl polyether, bis-N-cycloalkylpolyether, bis-N-aryl polyether bis-beta or alpha-amino acids or theirsalts in an amount to inhibit corrosion of said ferrous metals, whereinsaid Gemini surfactants have the formula

where: R₁ is independently a radical represented by —H or —CH₃, R₂ is analkyl, alkenyl chain, cycloalkyl or aryl; R₃ is a radical represented by—H, —CH₃, —CH═CH—CH₃, or —COOX; R₄ is a radical represented by —H, —CH₃,or —CH₂—COOX; R₅ is a radical represented by —H, an alkyl, alkenyl,cycloalkyl, aryl group, or a metal; R₆ is a radical represented by analkyl, alkenyl, cycloalkyl, or aryl group; n and m can have values from1 to 250, and i can have values of 0 and 1: when i=1: R₃ is a radicalrepresented by —H, —CH₃, —CH═CH—CH₃, or —COOX, and when i is equal to 0:R₃ is a radical represented by —COOX; In the radical —COOX used in R₃and R₄, X is represented by: —H, an alkyl, alkenyl group, a cycloalkylor aryl group, or a metal.
 25. The method of claim 24, wherein saidcorrosion inhibitor comprises 1 to 100 weight percent of said Geminisurfactant.
 26. The method of claim 24, wherein said corrosion inhibitorincludes a solvent selected from the group consisting of distilledwater, brine with a divalent ion selected from the group consisting ofcalcium, magnesium, strontium and barium, and organic compounds selectedfrom the group consisting of methanol, ethanol, isopropanol, xylene,toluene, diesel, gasoline or mixtures at a concentration of 1 to 99 wt%.
 27. The method of claim 24, wherein said corrosion inhibitor ispresent in an amount of 0.5 to 10,000 ppm.